From AI Proving Grounds to the Open Road: Using AI to Plan a Motorcycle Tour

At World Wide Technology, we spend a lot of time talking about how AI is transforming industries. From accelerating software delivery to making infrastructure self-healing, AI has become a cornerstone and primary focus of innovation for our customers. But sometimes, the best way to understand a technology is to step outside of the data center and put it to work in everyday life.

That's exactly what we did.

We're Dave King and Jeff Andiorio - two WWT technologists, two military veterans (Army and Air Force), and two motorcycle enthusiasts who share a love for automation, AI, and the open road. This September, we're heading out on a four-day motorcycle tour of New England. The journey will take us from Leesport, Pennsylvania, over to the Empty Sky Memorial, up through the mountains of New Hampshire, across Vermont's famous Route 100,down the coast of Maine, through Boston, and back again covering some of the most scenic roads and historic sites in the Northeast.

But here's the twist: we're letting AI do the heavy lifting when it comes to planning.

Why AI?

In our day jobs, AI often gets positioned as a tool for large-scale enterprise challenges. But what happens when you point it at something as personal (and as fun) as a road trip? We wanted to test just how far AI could go in supporting real-world planning, logistics, and creativity.

While the key is in the prompt and context details, it turns out AI can be a pretty good travel agent, personal assistant, and gear consultant all in one.

How We Used AI in Preparation

We tried numerous different AI Agents and models, but in the end landed on ChatGPT5 for our trip. ChatGPT allowed for the creation of projects and defining the context relevant data and all content or files in the project was referenced for each new prompt or request.

1. Packing Lists

Riding motorcycles means traveling light. There's no trunk space on a Harley-Davidson Street Glide or a BMW K1600B. We asked AI to help us generate packing lists tailored for a late-summer motorcycle trip in New England. The results went beyond just clothing—it reminded us to bring earplugs, tire repair kit, and even kickstand pucks for parking on soft ground. One favorite recommendation was zip ties and duct tape for emergency repairs (because do you really need anything else…). It's one less thing to stress about before the ride.

2. What to Purchase

From rain gear to hydration packs, AI surfaced ideas of what was worth investing in before the trip. It helped us compare pros and cons of different motorcycle luggage systems, suggested vegan-friendly travel snacks (important for Jeff), and even recommended first-aid kit essentials.

3. The Itinerary

This is where AI really shined. We started with a few must-see stops—Mount Washington, Vermont's Route 100, Boston, the Empty Sky Memorial, and even a favorite diner back in Allentown, PA. Then we asked AI to stitch it all together into a day-by-day itinerary, with around 250–300 miles of riding per day.

The AI-generated plan included:

Marriott hotel stays (to keep it comfortable and consistent)
Scenic backroads and motorcycle-friendly routes (avoiding interstates where possible)
Cultural and historic stops (military memorials, local landmarks, and points of interest)
Dining suggestions for both a vegan and a non-vegan traveler

It even worked in rest stops at just the right intervals—something every rider knows is critical on long days in the saddle.

The Bigger Picture

Sure, planning a motorcycle tour with AI is fun. But it's also a proof point. If AI can effectively plan the details of a complex road trip—balancing preferences, optimizing routes, and reducing manual overhead—it's easy to see how it scales to enterprise use cases.

For us, this trip is more than just a ride through New England. It's a way to experience AI outside of the lab, outside of work, and to show how practical and accessible it has become.

We'll be sharing updates from the road, including what worked, what didn't, and how AI held up as our co-pilot. For now, the engines are tuned, the itinerary is set, and we're ready to roll.

Stay tuned—next stop, the open road.

The Final AI Generated Route

After tweaking and iterating on the prompt, adding and removing points of interest, here is the final itinerary we will follow. Will there be hallucinations? Look for the follow-up blog to see how it all went.

🏍️ 4-Day New England Motorcycle Tour Itinerary

Start/End: Leesport, PA

Dates: September 11–14, 2025

Bikes: 2024 Harley Davidson Street Glide + 2024 BMW K1600B

Style: Backroads, county highways, minimal interstates

Daily Target: 250–300 miles

Day 1 — Thursday, Sept 11, 2025

Leesport, PA → Jersey City, NJ → Albany, NY (~280 miles)

10:00 AM – Depart Leesport, PA
Stop 1: Gems & Joe Café, Allentown, PA (breakfast/brunch).
Ride east via US-22 → NJ backroads avoiding I-78 where possible.
Midday Stop: Empty Sky 9/11 Memorial, Jersey City, NJ
- Pay respects on September 11. Stunning NYC skyline backdrop.
Afternoon Ride: North on scenic US-202 & NY-9D along the Hudson River.
- Cross Bear Mountain Bridge, one of the most scenic crossings in NY.
Evening Stop: Schuyler Mansion, Albany, NY (historic home of Revolutionary War General Philip Schuyler).
Overnight: Fairfield Inn & Suites Albany Downtown (Marriott)
Scenic ride east on PA-61 → PA-100 → backroads toward Allentown.

Day 2 — Friday, Sept 12, 2025

Albany, NY → Route 100 VT → Mount Washington, NH (~270 miles)

Morning Ride: Scenic cruise northeast on NY-7 → VT backroads.
Route 100, Vermont: One of America's best motorcycle roads. Rolling hills, small villages, foliage views.
Lunch Stop: The Mad Taco in Waitsfield, VT (vegan-friendly + hearty non-vegan).
Afternoon Ride: Cross into NH via scenic NH-112 (Kancamagus Highway).
Mount Washington Auto Road: Ride (weather permitting) or stop at the base.
Overnight: Fairfield Inn & Suites North Conway (Marriott)

Day 3 — Saturday, Sept 13, 2025

North Conway, NH → Portland, ME → Boston, MA (~280 miles)

Morning Ride: NH-302 east → coastal Maine.
Portland, ME Stop:
- Ride scenic US-1 Coastal Route for ocean views.
- Lunch at Green Elephant (famous vegan Asian bistro) and lobster for non-vegan at Portland Lobster Company.
Afternoon Ride: Continue US-1 south through Kennebunkport → Portsmouth → coastal Massachusetts.
Evening in Boston:
- Visit Freedom Trail highlights (Paul Revere House, Old North Church, USS Constitution).
- Dinner: Red White Ramen (vegan ramen bowls) or Union Oyster House (classic seafood).
Overnight: Courtyard by Marriott Boston Downtown

Day 4 — Sunday, Sept 14, 2025

Boston, MA → Western MA backroads → Leesport, PA (~300 miles)

Morning Ride: Head west on MA-2 (Mohawk Trail – scenic motorcycle road).
Midday Stop: Historic Deerfield, MA (colonial history + rest break).
Afternoon Ride: Continue through Berkshires → PA backroads.
Dinner Stop: Lancaster, PA (downtown vegan options like Root, plus Amish markets for local flavor).
Return to Leesport by 8:00 PM.

🔑 Highlights & Themes

Military/Historic: Empty Sky Memorial (9/11), Schuyler Mansion, Freedom Trail (Boston), Mount Washington (WWII training relevance).
Scenic Roads: Route 100 VT, Kancamagus Highway NH, US-1 Coastal Maine, Mohawk Trail MA.
Food Stops: Vegan + non-vegan options carefully balanced.
Mileage: All days ~270–300 miles, mostly scenic backroads.
Marriott Hotels: Used where available for comfort + consistency.